Details
Stereochemistry | MIXED |
Molecular Formula | C14H18N2O3 |
Molecular Weight | 262.3043 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 0 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCC#CC(C)C1(CC=C)C(=O)NC(=O)N(C)C1=O
InChI
InChIKey=NZXKDOXHBHYTKP-UHFFFAOYSA-N
InChI=1S/C14H18N2O3/c1-5-7-8-10(3)14(9-6-2)11(17)15-13(19)16(4)12(14)18/h6,10H,2,5,9H2,1,3-4H3,(H,15,17,19)
Methohexital is an ultrashort-acting barbiturate widely used in dentistry because of its rapid onset, predictable effects, and short duration of action. It was marked under the name brevital sodium for the intravenous anaesthesia. It has also been commonly used to induce deep sedation. Like other barbiturates, methohexital exerts its effects through the gamma-aminobutyric acid (GABA) receptor complex. By binding to its own receptor on the complex, methohexital augments the inhibitory effect of GABA on neurons and additionally can exert a similar effect independent of GABA.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18568113
Curator's Comment: SM Chernish’s group at Lilly Research Laboratories (Indianapolis, USA) in 1956.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2093872 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1842156 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Preventing | BREVITAL SODIUM Approved UseBrevital Sodium can be used in adults as follows: For intravenous induction of anesthesia prior to the use of other general anesthetic agents. For intravenous induction of anesthesia and as an adjunct to subpotent inhalational anesthetic agents (such as nitrous oxide in oxygen) for short surgical procedures; Brevital Sodium may be given by infusion or intermittent injection. For use along with other parenteral agents, usually narcotic analgesics, to supplement subpotent inhalational anesthetic agents (such as nitrous oxide in oxygen) for longer surgical procedures. As intravenous anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli (see WARNINGS ). As an agent for inducing a hypnotic state. Brevital Sodium can be used in pediatric patients older than 1 month as follows: For rectal or intramuscular induction of anesthesia prior to the use of other general anesthetic agents. For rectal or intramuscular induction of anesthesia and as an adjunct to subpotent inhalational anesthetic agents for short surgical procedures. As rectal or intramuscular anesthesia for short surgical, diagnostic, or therapeutic procedures associated with minimal painful stimuli. Launch Date1960 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4005094 |
25 mg/kg single, rectal dose: 25 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.39 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
2.24 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2.71 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
151 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566 |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
|
136 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
204 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2024566/ |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
102 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/4005094 |
25 mg/kg single, rectal dose: 25 mg/kg route of administration: Rectal experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: HEALTHY age: CHILD sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.1% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/17171861 |
1 % single, intravenous dose: 1 % route of administration: Intravenous experiment type: SINGLE co-administered: |
METHOHEXITAL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
30 mg/kg single, rectal Dose: 30 mg/kg Route: rectal Route: single Dose: 30 mg/kg Sources: |
unhealthy, 2.6 + 2.2 years n = 648 Health Status: unhealthy Age Group: 2.6 + 2.2 years Population Size: 648 Sources: |
Other AEs: Airways obstruction, Transient nocturnal oxygen desaturation... Other AEs: Airways obstruction (4%) Sources: Transient nocturnal oxygen desaturation (4%) |
2 mg/mL single, intravenous Dose: 2 mg/mL Route: intravenous Route: single Dose: 2 mg/mL Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Seizures, Hepatic dysfunction NOS... AEs leading to discontinuation/dose reduction: Seizures Sources: Hepatic dysfunction NOS (severe) Instability cardiovascular (severe) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Airways obstruction | 4% | 30 mg/kg single, rectal Dose: 30 mg/kg Route: rectal Route: single Dose: 30 mg/kg Sources: |
unhealthy, 2.6 + 2.2 years n = 648 Health Status: unhealthy Age Group: 2.6 + 2.2 years Population Size: 648 Sources: |
Transient nocturnal oxygen desaturation | 4% | 30 mg/kg single, rectal Dose: 30 mg/kg Route: rectal Route: single Dose: 30 mg/kg Sources: |
unhealthy, 2.6 + 2.2 years n = 648 Health Status: unhealthy Age Group: 2.6 + 2.2 years Population Size: 648 Sources: |
Seizures | Disc. AE | 2 mg/mL single, intravenous Dose: 2 mg/mL Route: intravenous Route: single Dose: 2 mg/mL Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Hepatic dysfunction NOS | severe Disc. AE |
2 mg/mL single, intravenous Dose: 2 mg/mL Route: intravenous Route: single Dose: 2 mg/mL Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Instability cardiovascular | severe Disc. AE |
2 mg/mL single, intravenous Dose: 2 mg/mL Route: intravenous Route: single Dose: 2 mg/mL Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.preprints.org/manuscript/202101.0503/v1 Page: 3.0 |
likely | |||
Sources: https://www.preprints.org/manuscript/202101.0503/v1 Page: 3.0 |
likely | |||
Sources: https://www.preprints.org/manuscript/202101.0503/v1 Page: 3.0 |
likely | |||
yes | ||||
Page: 1643.0 |
yes | |||
Page: 891.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 265.0 |
PubMed
Title | Date | PubMed |
---|---|---|
Placental transfer of tubocurarine. Case report. | 1968 Jun |
|
Clinical studies on induction agents. 28. A further comparison of venous complications following thiopentone, methohexitone and propanidid. | 1969 Aug |
|
Methohexitone and propanidid. A comparative investigation of the side effects. | 1969 Feb |
|
Factors in arrhythmia during dental outpatient general anesthesia. | 1970 Sep-Oct |
|
Methohexitone and thiopentone. Response to stimuli and incidence of some side effects. | 1971 Oct |
|
Activation of the electroencephalogram with intravenous Brietal (methohexitone): the findings in 100 cases. | 1971 Oct |
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A rare allergic reaction to sodium methohexital. | 1972 Dec |
|
Intramuscular sodium methohexital as a sole pediatric anesthetic-analgesic agent. | 1972 Nov-Dec |
|
A comparative study of etomidate and methohexital as induction agents for analgesic anesthesia. | 1976 |
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Identification of speech lateralization by intracarotid injection of methohexital. | 1978 Jul |
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Seizures induced by methohexital. | 1981 Apr |
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The prevention of pain on injection. A study of the effect of intravenous lignocaine before methohexitone. | 1981 Sep |
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[Electroclinical aspects of intramuscular methohexital anesthesia in children]. | 1982 Nov |
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Severe respiratory depression following pentazocine and methohexitone. A case report. | 1982 Oct |
|
Seizure duration in unilateral electroconvulsive therapy. A comparison of the anaesthetic agents etomidate and Althesin with methohexitone. | 1984 Jun |
|
Drugs as allergens: the molecular basis of IgE binding to thiopentone. | 1987 |
|
[Generalized seizure induced by methohexital]. | 1987 |
|
Pain on injection of methohexitone. The use of lignocaine to modify pain on injection of methohexitone during anaesthesia for electroconvulsive therapy. | 1989 Aug |
|
Rectal methohexital causing apnea in two patients with meningomyeloceles. | 1991 Jun |
|
Spontaneous seizure after concurrent use of methohexital anesthesia for electroconvulsive therapy and paroxetine: a case report. | 1995 Feb |
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A prospective study of rectal methohexital: efficacy and side effects in 648 cases. | 1995 Nov |
|
The comparative effects of methohexital, propofol, and etomidate for electroconvulsive therapy. | 1995 Sep |
|
A prospective evaluation of the safety and efficacy of methohexital in the emergency department. | 1996 Jul |
|
Alfentanil decreases the excitatory phenomena of sodium methohexital. | 1998 Sep |
|
Acute detoxification of opioid-addicted patients with naloxone during propofol or methohexital anesthesia: a comparison of withdrawal symptoms, neuroendocrine, metabolic, and cardiovascular patterns. | 2000 Apr |
|
Inhibition of activator protein 1 by barbiturates is mediated by differential effects on mitogen-activated protein kinases and the small G proteins ras and rac-1. | 2004 Dec |
|
Effect of testosterone replacement or duration of castration on baroreflex bradycardia in conscious rats. | 2005 Mar 30 |
|
Orchiectomy or androgen receptor blockade attenuates baroreflex-mediated bradycardia in conscious rats. | 2006 Jan 23 |
|
Seizures during intracarotid methohexital and amobarbital testing. | 2007 Feb |
|
Colorectal distension-induced pseudoaffective changes as indices of nociception in the anesthetized female rat: morphine and strain effects on visceral sensitivity. | 2007 Jul-Aug |
|
Pulmonary response to intratracheal instillation of ultrafine versus fine titanium dioxide: role of particle surface area. | 2008 Dec 1 |
|
Surface area of particle administered versus mass in determining the pulmonary toxicity of ultrafine and fine carbon black: comparison to ultrafine titanium dioxide. | 2009 May 4 |
|
Transient global amnesia after ablation of premature ventricular beats arising from the right coronary cusp. | 2010 Aug 15 |
Patents
Sample Use Guides
Dosage is highly individualized: the drug should be administered only by those completely familiar with its quantitative differences from other barbiturate anesthetics. Adult: brevital sodium (METHOHEXITAL SODIUM) is administered intravenously in a concentration of no higher than 1%. Higher concentrations markedly increase the incidence of muscular movements and irregularities in respiration and blood pressure.
Induction of anesthesia: a 1% solution is administered at a rate of about 1 mL/5 seconds. Gaseous anesthetics and/or skeletal muscle relaxants may be administered concomitantly. The dose required for induction may range from 50 to 120 mg or more but averages about 70 mg. The usual dosage in adults ranges from 1 to 1.5 mg/kg. The induction dose usually provides anesthesia for 5 to 7 minutes. Maintenance of anesthesia: may be accomplished by intermittent injections of the 1% solution or, more easily, by continuous intravenous drip of a 0.2% solution. Intermittent injections of about 20 to 40 mg (2 to 4 mL of a 1% solution) may be given as required, usually every 4 to 7 minutes. For continuous drip, the average rate of administration is about 3 mL of a 0.2% solution/minute (1 drop/second). The rate of flow must be individualized for each patient. For longer surgical procedures, gradual reduction in the rate of administration is recommended
Pediatric Patients: Brevital Sodium is administered intramuscularly in a 5% concentration and administered rectally as a 1% solution.
Induction of anesthesia: by the intramuscular route of administration, the usual dose ranges from 6.6 to 10 mg/kg of the 5% concentration. For rectal administration, the usual dose for induction is 25 mg/kg using the 1% solution.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9732376
To explore the mechanism by which methohexital (MTH) activates epileptiform activity in patients with epilepsy, it was examined the effects of MTH on hippocampal CA1 and neocortical neurons via extracellular and whole-cell patch-clamp recordings in rat brain slices. Perfusion of slices with 10 to 100 microM MTH caused no significant change in glutamatergic transmission in the hippocampal CA1 region, but enhanced gamma-aminobutyric acid (GABA)A-mediated inhibitory postsynaptic currents and induced spontaneous inhibitory postsynaptic currents in neocortical and hippocampal CA1 neurons. In addition, MTH induced a tonic, bicuculline-sensitive hyperpolarization in association with increases in membrane conductance, suggesting a direct stimulation of GABAA receptors by MTH. Spontaneous epileptiform activity was not observed in the neocortex and hippocampus after exposure of slices to MTH, neither in the standard in vitro condition nor in the presence of 4-aminopyridine, which promotes rhythmic synaptic activities.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67084
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N01AF01
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WHO-VATC |
QN05CA15
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QN01AF01
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N0000175693
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N0000008016
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DEA NO. |
2264
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N05CA15
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METHOHEXITAL
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DB00474
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6847
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CHEMBL7413
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Methohexital
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102216
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m7323
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DTXSID1023287
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D008723
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)